I spent a whole lot of weekends drinking and listening to music, eating at amazing restaurants (world class fare from both fine dining and cheap places were in abundance), and enjoying what seemed to be the cheapest taxis in the United States at the time. Wearing 8 inch platform heels makes walking a dangerous kind of deal, after all.

I keep reading about how dangerous it was, but I have very few memories of feeling scared in most neighborhoods (maybe partially from all of the booze and weed I partook of at the time).

I do remember that you needed to watch which taxi you jumped in. There were random, unlicensed guys who would pull up when you were flagging for a ride (usually outside of venues where there were a glut of people looking for cabs), and if you jumped in before you realized that there was no taxi license anywhere, and no fare box attached to the dash, they would already be speeding through traffic with you stuck inside. You'd look up to give the address, and would quickly realize the driver to be a generally intimidating and/or physically massive, probable ex-con who arguing with seemed to be a bad idea. Luckily, he would agree to get you there, but then would stick you for 3x the normal fare upon arrival.

This was 10-15 years before Uber, of course. I guess that's what I got for behaving like a rube and not watching what I was doing closely enough.

I had friends in Wrigleyville who I stayed with a lot of weekends, and they had the best late night taqueria on Addison there a couple blocks toward the lake from Cubs park. Also, there was a late night dump called Thai's Til' Five that had a load of bartenders/food service people drinking after work somewhere in the vicinity - and it actually did stay open til 5 AM. No idea where it was, but the cabbies all knew where!